While escorting two Helotes Gang members to jail by rail, the U.S. marshal for the Western District of Texas acted the perfect gentleman—and paid the ultimate price.

“How they peppered us!” Jim Pitts complained as he and Charlie Yeager leaped from the International & Great Northern express train a few miles north of New Braunfels, Texas. “I am full of holes!” It was true enough— varying accounts place between three and seven lead slugs in Pitts’ body as he and Yeager hit the ground and began running. The words would be his last. Before they’d made it 90 feet, Pitts sank to the ground. Yeager dragged him a few yards farther then eased down beside his dying partner. He had no choice; heavy steel manacles linked their wrists together. Yeager had always looked up to the older Pitts, but survival instinct trumped hero worship. As he pondered how to get free of his fix, he spied a large, sharp-edged rock—not so heavy it could shatter steel links, but plenty enough to bash through meat, cartilage and bone.

It’s tough to feel sorry for Pitts. He was fleeing a rightful prison sentence and had left several dead or, for all he knew or cared, dying people aboard the train. A string of bad choices made of his own free will had led him to this end. Still, he’d likely have breathed a few years longer—albeit the rank air of a prison cell—were it not for the well-meaning but ill-considered actions of the lawman in charge of ferrying him and Yeager to the pen in February 1885.

Harrington Lee “Hal” Gosling wasn’t a career peace officer. The Tennessee native and Annapolis graduate was an attorney and journalist. Former editor/publisher of The Quill in Castroville, Texas, Gosling’s active participation in Republican politics had garnered him an 1882 appointment as U.S. marshal for the Western District of Texas. A genial sort by all accounts, he was, according to one friend, “a big, bluff, kindly, rollicking daredevil, afraid of nothing.” If such a learned lawman had remembered his Shakespeare, Falstaff’s admonition that “the better part of valor is discretion” might have served him well. For whether his kind nature, his fearlessness or both were to blame, Hal Gosling’s gross errors in judgment would cost three lives, one of them his own.

James B. Pitts (aka Tom Pitts or Jim Hall/Hale) and Charles Yeager were nobody’s idea of kindly. A 30ish career criminal who’d reportedly served prison time alongside John Wesley Hardin, Pitts was described in news accounts as “an old road agent, train robber and murderer, and a man of undoubted nerve.” At 23, Charlie Yeager was his eager apprentice and accomplice, called by a fellow outlaw “Pitts’ tool, the lesser villain in every way.” The pair ran with a confederation of miscreants known variously as the Robbers’ Cave Gang or the Helotes Gang. They were thieving, murdering thugs, described in the newspapers as “young in years but old in crime.” The gang had torn a bloody swath across south Texas throughout the early 1880s, and one recent caper, the robbery of a post office at Smithwick, 50 miles northwest of Austin, had landed Pitts and Yeager in the U.S. District Court in Austin. There, on the morning of February 21, 1885, they were convicted of robbery and each sentenced to life terms. Judge Ezekiel B. Turner charged U.S. Marshal Hal Gosling with escorting Pitts and Yeager from Austin to the San Antonio jail, thence to the federal penitentiary at Chester, Ill.

Unlike the usual U.S. marshal of his time, Gosling was no pencil pusher who left the fieldwork to deputies. He would personally lead the escort detail and chose Deputy U.S. Marshals John Manning and Fred Loring to accompany him. Manning was an experienced hand, described in one account as “sober, gentlemanly, reliable,” yet a man who “would rather fight than eat.” Loring had experience not only as a deputy but also as a train conductor—knowledge that would prove handy before this assignment was over.

During the trial several female relatives had sat at the railing behind the defendants. Throughout the proceedings the two men conversed in whispers with Pitts’ wife of four months, Melissa; her sister, Annie Scott; Pitts’ grandmother, Elizabeth Drown; and Yeager’s sister, Rosa Yeager. A bulky matron of about 60, Drown was said to have offered her home as a hideout for the Helotes Gang. Annie Scott and Rosa Yeager were still in their teens; Melissa Pitts was only slightly older.

After sentence was pronounced, Manning handcuffed Pitts and Yeager together and walked them into the grand jury room. A sympathetic Gosling permitted the women to wait with them while he made transportation arrangements. Here, more murmured communications took place. Another deputy, Gordon Walker, warned Gosling he feared the group was plotting an escape. The defendants’ own lawyer, M.G. “Mac” Anderson, expressed similar suspicions to Judge Turner, concerned “that no part in the performance should be attributed to him.” Gosling paid their cautions little mind, except to have Walker and another deputy accompany his group to the railroad depot, where they’d board the late train for San Antonio. On the way they stopped at Salges’ Chop House where Gosling, ever the gentleman, treated the prisoners to a costly dinner.

Manning had observed the whispered courtroom conferences and noted the presence in court of more of the defendants’ relations and friends, including several hard case pals. His keen law dog sense smelled trouble, especially when Gosling admitted he’d given Carroll Brannon their itinerary. Carroll’s brothers Joe and Dick were among the worst of the Helotes bunch; Dick was currently standing trial for his part in the Smithwick post office robbery, while Joe was on the dodge in Missouri.

When Manning learned that many of these folks—Carroll Brannon among them—planned to board the same train, he urged Gosling to postpone the trip until the next day. Gosling waved this off as he had the earlier warnings. To Manning’s dismay the marshal even ordered the deputy to unshackle the prisoners in the restaurant, that they might eat in comfort. After the meal was finished, as Manning prepared to cuff the prisoners together again, Pitts presented his left hand, Yeager his right. Manning balked—they’d had the opposite wrists connected earlier. Pitts pleaded a sore wrist, so Manning grudgingly complied.

At the depot, the lawmen found the Pitts and Yeager contingent ready to board. Melissa Pitts tearfully begged Gosling’s permission to ride to San Antonio alongside her husband. Chivalry and compassion again got the better of Gosling’s common sense; he agreed that the ladies in the party, plus several of the men, might share the smoking car with the lawmen and their prisoners. The motley group climbed aboard. Near the rear of the smoker, bench seats on either side of the aisle were turned facing each other. On the right side, the marshals seated Pitts and Yeager against the wall, facing one another, their manacled arms reaching across the space between the benches. Melissa Pitts sat beside her husband, Rosa Yeager next to her brother. As they boarded, Grandmother Drown indicated the seat just behind Pitts and begged Gosling’s permission to occupy it. The affable Gosling consented, and even “assisted the old vixen” to her requested place, seating Annie Scott beside her on the aisle.

Across the aisle, Gosling and Loring took the facing aisle seats, and Manning took the window seat next to Loring. Gosling’s friend Will Lambert, a former newspaperman and chief clerk of the state Legislature, happened to be aboard, returning from business in Austin. At Gosling’s invitation Lambert took the window seat beside him. Beyond them sat the other assorted Pitts-Yeager followers, with Carroll Brannon several rows ahead in the car’s front row. Gosling, at least, apparently found the seating arrangement tactically sound. He faced Yeager, if on the oblique, and could view the others of the party beyond, all the way to Brannon. His deputies likewise faced Pitts. Thus, both prisoners were in view, and the lawmen could easily foresee any danger. Or so Gosling thought.

The train pulled out at about 4:30 p.m. on February 21. All went smoothly for the first hour and a half of the journey. The Pitts’ whispered conference behind a newspaper seemed to raise no concern. Melissa Pitts and Rosa Yeager cried much of the way and hung about the necks of the prisoners, but this seemed natural; Pitts and his wife were still newlyweds, and the men were going away for a very long time, likely for good. As the train neared New Braunfels, little more than halfway between Austin and San Antonio, the two women abruptly repaired to the adjoining ladies’ car, carrying with them a small black valise. Lambert and Loring were watching but expressed no suspicion. When the women returned several minutes later, they were without their piece of luggage and looking “sad, as though going to a funeral.”

If Gosling or the others found any of this behavior worrisome, it didn’t show. Though Gosling had stepped out on the platform at every stop to ensure, according to Lambert’s later statements, “that no allies of the prisoners were at the station to aid any attempt at rescue,” the marshal appeared at ease with the known confederates inside the smoking car. In Lambert’s view Gosling treated his prisoners “more like friends than a brace of the most villainous desperadoes ever consigned to the keeping of an officer.” To the ladies he showed “a manner becoming a Chesterfield.” Perhaps the ladies’ presence put the lawmen at ease, for while they focused some vigilance on the men, they paid scant attention to the women. Unfortunately, it seems this was just what the Pitts-Yeager crew was counting on.

When the ladies returned to the car, their displays of grief became downright histrionic. They sobbed and hugged the men so tightly the prisoners’ hands disappeared among the billows of their bustled skirts. Manning saw it first—Pitts’ free hand emerging from the folds of his wife’s skirt clutching a revolver. What happened next took place in an instant, which accounts for some confusion among the various accounts. Lambert heard a noise from the aisle, Loring saw a shadow, and both turned to see Pitts and Yeager rising, each brandishing a pistol in his free hand. Before anyone could react, Pitts snapped, “Hands up, gentlemen!”

Gosling looked at Lambert and said, “Well, I didn’t believe they’d try it,” as he rose to stand. Suddenly, two pistol shots rang out, and the trusting marshal pitched forward across Lambert’s and Manning’s laps, a bullet in his head. Lambert noticed that his lifeless hand gripped the butt of a pistol tucked inside his waistband, trapped beneath his vest.

Loring left his seat shooting. Manning, wounded in the first volley and briefly pinned by Gosling’s inert form, quickly got his own revolver into action. The firing then “grew general,” Lambert recalled, adding, “The pistol shots were incessant, and the smoke filled the compartment so densely it was almost impossible to see the forms of the men.” No stranger to gun battles, having served as both a Texas Ranger fighting Indians and a Confederate soldier battling Union troops, Lambert later said, “I never heard bullets whistle or hit like they did in that car the night poor Hal Gosling was killed by one of his prisoners.”

The two deputies fought side by side, the prisoners returning fire and pressing them toward the ladies’ car. A shot from Manning struck Yeager in the neck. Manning, by now hit in both the neck and shoulder, fired until his pistol was empty. As he backed up a couple of rows to reload, his ejector jammed. A model of cool under fire, Manning squatted down, snatched a pencil from his vest pocket and used it to punch out the empty casings. Lambert, who was unarmed, sought refuge in the ladies’ car. Loring emptied his pistol and retreated into that car to reload. Manning finished reloading, shot until empty a second time and was falling back to reload again when the two prisoners charged him and thrust their pistol barrels against his body. Manning just managed to deflect them as they fired, getting his face and coat scorched in the process but avoiding further wounds.

Hearing the ruckus, the train conductor charged in from the forward car, armed with a handgun. Seeing Drown level a pistol in Gosling’s direction and then swing it toward him, the conductor gut-shot the old warhorse. Rosa Yeager took a stray bullet from someone’s pistol and also went down.

As Manning fended off the two outlaws, they shoved past him, wrestled open the smoker’s rear door and, with the express train still moving at 30 or 40 miles per hour, leaped out. They tumbled onto the roadbed, clambered to their feet and disappeared into the night.

Loring and Lambert re-entered just after Pitts and Yeager had jumped and found the smoking car a bloody mess. Gosling was sprawled dead across a seat, one bullet hole behind his left ear, another in his back. Manning was bleeding badly from his wounds and weakening. Drown lay dying, a .45 revolver beneath her seat. Rosa Yeager had an ugly wound in the right thigh, and the conductor had a bullet crease in his forehead. Lambert later claimed the participants had fired at least 50 shots in the car. Taking the various statements into account, his estimate is likely dead on.

Among the combatants Loring alone was uninjured, and he now took charge. Having been a conductor, he knew to use the pull cord to stop the train. He left Lambert and the conductor to tend the wounded, hopped off and made a quick but fruitless search for Pitts and Yeager. Loring then returned to the train, and he and the conductor “made prisoners of the whole Pitts-Yeager ‘layout.’”

The train double-timed it into New Braunfels, where the injured received attention, and Loring turned over his prisoners to the Bexar County sheriff. Manning was made comfortable in a sleeping car, and he and Lambert took the train, and Gosling’s body, on into San Antonio, where they arrived about 11 p.m. Loring immediately organized a posse, which rode off to hunt the escaped convicts. At least two more posses headed out. Leading one group of deputy sheriffs was Gosling’s old friend Texas Ranger Captain (and also a deputy U.S. marshal under Gosling) Josephus Shely.

Drown died later that evening, maintaining her innocence to the last and pleading to be buried alongside her grandson. She and outlaw Pitts would be planted side by side in New Braunfels the next day.

Shely’s posse found Yeager the next morning, several miles from the fatal scene, with bullet wounds in his neck and shoulder. He led the posse to Pitts’ body, lying in a weed patch near where they’d bailed out. Pitts left forearm was horribly mangled, the hand missing; thus had Yeager used that sharp rock he’d found to separate himself from his pal.

Yeager made a lengthy statement about what had occurred, fixing blame for the bloody escape on his dead partner. Pitts had smuggled the weapons aboard in his boots, Yeager claimed (no doubt to shield his sister), and had threatened Yeager to aid him or be the first casualty. He swore Pitts had shot Gosling, admitting only that when the shooting started, “I followed, keeping up a fire with my left hand, my right hand being handcuffed to Pitts.”

The posse abandoned plans to take Yeager into San Antonio on learning of “the excited state of feeling” there. Instead, they took him to the jail at New Braunfels, where the others were being held. It was a wise move; Hal Gosling had been well liked and respected and left a wife and two young sons. By the following day talk of a lynching was making the rounds all the way to New Braunfels. The sheriff detailed 16 deputies to watch over the prisoners and dissuade any vigilante action.

Gosling was buried in San Antonio on February 23. The Galveston Daily News reported that “strong men wept as bitterly as the ladies,” though it pulled no punches when it noted “the deplorable tragedy is largely due to Mr. Gosling’s own almost criminal carelessness.”

The kindly late Marshal Gosling rode to the Knights of Pythias Cemetery in a four-horse hearse, which headed a stately procession of mounted police, U.S. cavalrymen and light artillerymen, the 8th Cavalry band, two rifle units, multiple fire companies and numerous dignitaries. Among the pallbearers was Joe Shely. With Gosling laid to rest, it only remained to bring his killers to justice.

On February 27 Yeager and the others held in Gosling’s murder faced a preliminary hearing in New Braunfels. Manning, still bedridden but improving, was absent. District Attorney Eugene Digges read affidavits before Justice of the Peace James Aveline charging Charles Yeager, Celestine Yeager (Charlie’s brother), Rosa Yeager, Melissa Pitts, Annie Scott, T.J. Scott (Pitts’ father-in-law), Carroll Brannon, William Hardeman and Carl and Emile Krant (other members of the Robbers’ Cave bunch) with the murder of Marshal Harrington Lee Gosling.

Mac Anderson, again defending Charlie Yeager, waived examination on his client’s part and entered not guilty pleas for all the others. Loring gave a straightforward account of the incidents, beginning with Pitts and Yeager’s trial and concluding with the arrest of the defendants after the shootings. Will Lambert’s testimony was brief; he stated that he left the car after the firing commenced, and that when he returned, Gosling was already dead. In all, nine prosecution witnesses testified over two days. Some of the most damning testimony came from aptly named jailhouse informant James Leak, who had shared a cell with Pitts and Yeager for several days during their robbery trial. Leak testified that Melissa Pitts and Rosa Yeager had visited the two men regularly, and that he heard the group planning Gosling’s killing. He named Melissa Pitts “the sole hatcher of the plot” and said she “begged and plead [sic] with her husband and Yeager to make one effort for liberty.” Pitts, Leak said, wanted no part of the scheme, but “cried bitterly over [Gosling’s] arranged taking off.”

By March 28 Manning was well enough to testify at a habeas corpus hearing in San Antonio. The deputy corroborated Loring’s and Lambert’s statements, bluntly detailed Gosling’s egregious lapses in judgment and testified he saw Pitts obtain a pistol from his wife. Manning also claimed someone snapped a shot at him from near the front of the car as Pitts and Yeager jumped out, though he couldn’t identify the shooter.

The judge fixed bail for Carroll Brannon and Rosa Yeager, but they were unable to pay it. So they and the other defendants were bound over for trial in June, for which a special judge was selected (Judge Thomas Paschal, who would normally have heard the case, was Hal Gosling’s brother-in-law). Judge L.D. Denman immediately continued the case until December, when it was further continued until June 1886. In the meantime, a series of events involving the Helotes Gang and their circle eclipsed the Gosling murder, possibly burying the case for good.

Around the time of the first continuance, Jim McDaniel, another Helotes Gang member awaiting a federal prison term for mail robbery, had broken jail in San Antonio. On the first of July he was run to ground and killed in a fierce gun battle with Deputy Sheriffs James Van Riper and Ed Stevens, both members of the posse that had captured Charlie Yeager. In early August, Yeager and Dick Brannon (convicted in March for his part in the Smithwick robbery) made a daring, if short-lived, jailbreak from the county lockup in Austin. Neither made it more than a few hundred yards. A pursuing crowd quickly cornered Brannon, who, despite being armed with a pistol taken from the jailer, meekly surrendered. Yeager tried to stand off his pursuers with an ax he’d snatched up. When the well-heeled group explained the folly of bringing an ax to a gunfight, Yeager conceded the point. The escapees were hauled back to their cells, and shortly afterward Yeager made his long-delayed trip to the federal pen at Chester, Ill.

Around June 1, 1886, local lawmen got word that Joe Brannon had returned from Missouri. Under indictment in the Gosling murder and suspected in a string of other crimes, Brannon was very much wanted. Deputy James Van Riper and his brother William (also a deputy sheriff) set out for Carroll Brannon’s place, where they expected to find his fugitive brother. To help identify the outlaw they took along Frank Scott, Melissa Pitts’ brother and a Bexar County constable.

Joe Brannon was indeed there. When confronted, he broke for cover while firing on the lawmen. In the hot skirmish that ensued, a well-placed Winchester shot sheared off Brannon’s trigger finger. The unfazed outlaw quickly performed the famous “border shift.” Passing his gun to his left hand and bracing it with his mangled right, Joe continued blazing away. After swapping a dozen more shots with Brannon, the deputies rushed his position and found the outlaw shot through the lungs and bleeding to death.

Within weeks Frank Scott was himself in irons, indicted for murder. Local handyman Frank Harris had unwisely courted Annie Scott against the express wishes of her brother Frank and brother-in-law Jim Pitts. Harris had disappeared the previous September. His skeleton was found months later in a cave near Carroll Brannon’s property, a bullet hole through the back of the skull. The Harris murder case again involved witnesses from both the Scott and Brannon families, this time on opposing sides. Since Gosling’s death, there had been bad blood between the Scotts and Brannons. Mary Brannon (Carroll’s wife and Jim Pitts’ sister) blamed Melissa Pitts and her Scott relations for Jim’s death. Carroll blamed Frank Scott for his brother Joe’s death. The Brannons were therefore more than happy to testify against Frank Scott. He was convicted and given a life term.

With Joe Brannon and Jim McDaniel dead (along with Jim Pitts and Grandmother Drown), Yeager, Dick Brannon and Frank Scott in prison, and the Scotts and Brannons no longer on friendly terms, the Helotes Gang was effectively out of business. Perhaps it seemed redundant to spend state resources to prosecute Charlie Yeager; he was already facing a life stretch in the pen, and Pitts, whom most witnesses agreed had killed Hal Gosling, was sleeping beneath the Texas sod. Whatever the reasoning, Yeager and the others never stood trial for Gosling’s murder.

In December 1903 Charles Yeager received an unexpected early Christmas gift. Rosa Yeager, now Mrs. Leo Ichter, had for nearly two decades vigorously petitioned Washington for her brother’s release from prison. As an eyewitness to Gosling’s murder, she swore Pitts had done the deadly deed. An affidavit from none other than Gosling’s former deputy Fred Loring bolstered her claim. Her lengthy campaign paid off; President Theodore Roosevelt signed the pardon on December 23, and Yeager spent his holidays a free man. He returned to south Texas, vowing “to show his friends that he could and would be a good citizen.”

Charlie Yeager seems to have kept his promise. When the onetime outlaw died on January 15, 1931, the San Antonio newspapers mentioned only that he was “a native of San Antonio” and “an employee of the city park department.” Long forgotten, or maybe forgiven, were his lengthy prison term, his hell-bent younger days as a Helotes Gang outlaw and his role in the murder on a train of a too-decent-for-his-own-good U.S. marshal.

A frequent contributor to Wild West magazine and a member of Western Writers of America, J.R. Sanders [www.jrsanders .com], who writes from Redlands, Calif., adapted this article about the shooting of Hal Gosling and the aftermath from his book Some Gave All: Forgotten Old West Lawmen Who Died With Their Boots On, which is due out in January 2014 and is suggested for further reading.

Originally published in the December 2013 issue of Wild West. To subscribe, click here.

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